OK, here we go: This month’s column is dedicated to anal play. Still with me? Great, because an increasing number of couples—and at least one Girls character this season (we’re looking at you, Marnie)—are exploring the sexual delights that both men and women can find around back. You might be among them! Or you might be wondering: Are guys really that fixated on butt stuff? (According to our survey, yes: 67 percent of guys are open to anal play in some form.) And if they are into it, why? I’m here to explain. The Obvious Reason: It Feels Good First, a little anatomy refresher: Just like our sex organs, our anuses have thousands of nerve endings that respond to stimulation. I learned this firsthand in my twenties when, after several drinks at a bar, I went home with an old college friend. We fooled around for a while, and then I suddenly found myself on all fours as she used her hands up front and stuck her tongue where the sun don’t shine. I was as surprised as you are— that was part of the appeal— but it was incredible. One of my top three Lifetime Sexual Experiences (I admit read more

Jake has a girlfriend. But she’s in...wait for it...Australia. How he’s dealing could teach us all something about love. So, readers, your Jake is in love. Yes, it was just over a year ago that I began writing this column, still reeling from my divorce. Now I’ve gone and said those three magic words. To a woman who is not my grandmother! And best of all, they were reciprocated. Of course it’s complicated: She lives in Australia, and I’m still here in Los Angeles. Also, this ain’t my first long-distance rodeo; things with my ex began as a long-distance relationship, so my friends are, well, curious about this apparent pattern of mine. But I’ve come to learn that living continents away from someone doesn’t have to be an impediment to love. Here’s why. It Ends the Games I met the woman I’ll call Olivia (after my childhood crush Olivia Newton-John) when I was visiting a friend in Australia. We spent an incredibly fun week exploring Sydney together. Would we have jumped right in if we lived in the same city? Probably not. But the usual games (one date per week, etc.) didn’t apply, and without them we fell for each read more

“Balls. What to do with them?” a reader wrote in to ask me recently. (Funny thing, I often ask myself that very question!) So for this month’s column, I thought I’d shine a light, so to speak, on the things that make you go “Hmm,” straight from my Dear Jake inbox... Why are guys so obsessed with anal sex? Well, when you give a massage, don’t you tend to rub where and how you’d like to be rubbed? Same applies for anal. Guys get pleasure from having things (your finger, ideally; no sharp nails, please) in their ass, so they assume you’ll feel the same. And for some women (not all), it is pleasurable. Plus, it’s novel and a little taboo—performing anal is like having a sanctioned affair. We’re cheating on your front with your behind. Period sex: What do guys think? Just ask. Depends on the guy. Personally, I don’t mind at all. I’ll grab a towel, and then we have amazing, extra wet, extra hot sex (many women I’ve been with have reported that they are horniest during that time of the month). My squeamish friend Henry,* however, is not a fan. “I can’t watch horror movies, and read more

Jake explains what the hell they’re thinking (and how to avoid becoming tab #352). A story recently went viral on Reddit about a woman who’d posted her husband’s spreadsheet tracking seven weeks of his attempts to have sex—and her seven weeks of reasons for saying no. (For the record, they Did It three times; the rejections were variations on “I feel gross” and “I’m trying to watch a movie.”) Before I embark on a series of puns involving “spread” and “sheets,” I’ll pose the obvious question: Is keeping a spreadsheet a male thing? Do men (normal men, who aren’t serial killers or assholes) keep score? The answer is yes and yes. Here’s why: We want to remember the details. A few years ago another tale made the rounds about an NYC finance guy who kept a dating spreadsheet, with notes like, “Great bod—works in my building” and “Drunkenly hooked up...after karaoke.” The man defended himself on jezebel.com, saying, “I work long days, go to the gym, go out on dates, get home late...how am I going to remember them? This was an attempt to stay organized.” I’m guessing he’s still single. But my friend Ryan* is not. And before Ryan read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Hey, Jake, So I am friends with a guy, and we started sleeping together months ago. When we started sleeping together, he stopped sleeping with other people (he said by choice). He's pretty jaded from his ex because they didn't use protection, and he found out she had been cheating on him. Since then, he's always been strict on using protection. Well, now he doesn't want to use protection with me. There is that romantic chemistry there, but I want to understand it from his perspective. His ex was the only person he ever didn't use protection with, and this was over a year ago. Does he just miss the feeling, or is he sending monogamous vibes my way? Thanks, Willa Hi, Willa, So many of the questions I receive require such a simple answer: Talk to him! I mean, look, if you’re doing the most intimate thing I can thing of next to shopping for a puppy, then surely you read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Hi, Jake, So, I like this guy—a lot, actually—the only problem is that he has a girlfriend. However, he flirts (or so I assume) relentlessly with me. Even my best friend says he talks to me and acts a certain way with only me and no one else. He makes comments like he hates when I'm not around because it's boring and says if we went out he'd buy me drinks. We have these amazing conversations. Am I just thinking too into it? I don't want to ask him myself because I'm not the type of girl to break up a relationship, but I'm so curious to know what he may be thinking. Can you offer me some input? Thank you so much, Danielle Hi, Danielle, There are only two ways to find out what this guy is thinking. 1) Break into his email and read everything he’s every written about you and/or the girlfriend, or 2) talk to him. As read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Hey, Jake, Sex Q for you: How do you tell someone with more experience than you (read: their "number" is higher) that they're fairly incompetent while fooling around? Is there a nice way to correct what they're doing? Thanks! Julie Hi, Julie, Great question! It’s funny—I was just dating someone for a few weeks who clearly knew what she wanted in bed but didn’t know the right way to express it. She was so clinical about her instructions, as if she were telling me how to use a complicated espresso maker, it was an immediate turn-off. I mean, guys want to know what’s working and what’s not, but there’s a way to keep it sexy. Jake’s advice: Start with positive reinforcement. Men are like puppies—we respond much better to encouraging feedback than negative. If something feels good, let him know with an “Ooh, yes, that feels good,” kind of thing (it’s like our version of a Scooby snack). If it doesn’t read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Hi Jake, I haven't been in a relationship for three years, and I like it except when my parents keeping saying to just find a man and get married. Recently I hit on a man who I think is really into my type, and we really get into a long conversations—though we haven't met yet. We're going on a blind date, so should I behave restrained, shy, and reserved when I meet him? Or should I really start using makeup and get myself "like a butterfly" to attract him? Hi, I don’t think you should try to behave a certain kind of way or pretend to be something you’re not. These three words may sound cliche, but they are totally true: Just be yourself. Now, this is not to say you can’t doll yourself up a bit for the date—I just wouldn’t dress up like someone that’s not you. If you’re most comfortable in a cute T-shirt and jeans, then wear read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Dear Jake, I’m currently dating a man, and it's only been close to three months, but he seems to be way more into the relationship than myself. We’ve known each other for a long time, but were out of touch for about five years before we reconnected a few months ago. He is a great guy—the kind of guy I would want to settle down with—but I’m not “feeling it.” I like him as a person and enjoy spending time together, but we both have kids and busy work schedules. I’m afraid that the pressure from those things may be what's holding me back, or it may be because I know he is way more into our relationship. He keeps telling me that he has wanted this for so long, so I’m really starting to feel pressure and like he has high expectations of me and us as a couple. How should I let him know that I’m just not where read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Dear Jake, My boyfriend and I have been dating for three months. Recently, he revealed that he is extremely sexually frustrated. I know I'm not ready to have sex with him. We do other things, but I can never satisfy him. Is this relationship doomed? He is worried he is going to do something he may regret, but I'm not going to give in to something I'm not comfortable with just to make him happy. I don't feel as if he is pressuring me—we just want to find a solution to this current problem in our relationship. I'm starting to feel guilty that I get him revved up with no release, but it also seems cruel to cut off any physical intimacy. I'm really confused. Any advice? —Sam Hi, Sam, I don’t know how old you are, but I’ll admit that I didn’t have sex until I was 18. My girlfriend and I had dated for almost six months before we read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Hi, Jake, I recently started a new job, and my husband and I now work opposite schedules most of the time. We sometimes go days at a time without seeing the other person awake, and it's hard for us to stay connected. Then when we do get time together, there's a lot of pressure for it to be amazing. Any advice for how to handle this relationship lifestyle? Lately I've been feeling really frustrated by it. Thanks, Emilie Dear Emilie, That does sound really frustrating. One of the most important lessons I learned from being married is that you have to keep having sex. And the longer you wait, as you note, the more the expectations build into something neither of you can live up to. My advice is to figure out a way to surprise him with sex. Even if he’s tired, if you wake him up to have sex with him, he’ll appreciate it. It doesn’t have to be read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com. Hi, Jake, So this man has been flirting with me seriously the last two weeks. But here is the thing: The man won't, rather doesn't, touch me. When we are close, you'd think he'd even touch my arm, but nothing! What gives? Kind regards, Felly Dear Felly, Jake firmly believes that flirting involves a little arm touching. So my question is, how do you know he’s flirting? And, if you like the guy, don’t assume it’s his job to make that physical leap. Some guys are just shy. Guys like a woman who expresses what she wants. If you’re into him, let him know. Maybe he’s just waiting for permission (either verbal or physical) before he makes a move. —Jake For more advice, download Glamour's digital edition or pick up an issue on newsstands now. P.S. Do you have dating or relationship questions for Jake? Ask in the comments below, tweet him @glamour_jake, or email smittenbloggers@gmail.com. read more

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamourmag_jake or via email smittenbloggers@gmail.com. Hi, Jake, OK, here's the deal: There is this guy I've known since we were in diapers, and we used to be really close. Recently, he came out of nowhere and started asking to hang out. He is known to be a player and all that, and I know that he isn't quite over his last girlfriend. (That's a whole different story altogether...) Anyway, he comes to me for advice about girls and what-not, but I feel like he isn't just seeking "advice"—if you know what I mean... Am I reading into it too much, or is there something legit going on here? Thanks, Ash Dear Ash, I hate to state the obvious here, but I think the only way for you to know is to ask him. Surely if you’ve known him since you two were in diapers, you’re close enough to ask him straight-up what his deal is. The important thing, I think, is for you to know what read more